It conducts outreach programs that range from talks to demonstrations to workshops, and it collaborates with educational institutions and many other historic organizations and individuals in Dutchess County.

The Historical Society is funded through membership dues, the sales of its Yearbook and publications, solicitation of grants, and through philanthropic gifts and is a US tax exempt Charitable Organization.

He laid out his vision for the Society in a letter dated December 10, 1914, mentioning a number of elements which came to fruition including an annual yearbook, occasional publications, and transcriptions of cemetery headstones.

[13] The Collections include archival items, photographs, postcards, textiles,[14] diaries, will, deeds, needlework, clothing, genealogical information, and correspondence within its house museum.

There is a collection of books, articles and private letters of historian and illustrator Benson Lossing, who was born in the town of Beekman, lived for some time in Poughkeepsie, and eventually built a home and library in Dover.